This article describes how researchers used a culturally responsive case study approach to understand how Native Hawaiian students made postsecondary decisions and the lessons they learned through this process. Unique to this study were the steps taken in gaining entry to the research site and building relationships with the gatekeepers and student participants through culturally appropriate communication styles and activities. Concerted efforts were employed prior to and during the interviews to promote culturally responsive interactions (e.g., sharing of food). Implications are discussed for individuals teaching, counseling, and researching Native Hawaiian students and their families and include strategies for building relationships to gain entry and to gain confidence of participants; investigating social context prior to entry, discussion of rituals and routines, values and priorities; and viewing participant responses with respect to their worldview.